A Definitive Ranking Of The Lonely Island’s 10 Best Songs
From 'Lazy Sunday' to 'I Just Had Sex', which track reigns supreme?
The Lonely Island have spent the last decade producing some of the greatest comedic music of our generation.
Comedic trio Andy Samberg, Jorma Taccone and Akiva Schaffer, have been producing music as The Lonely Island since 2001. Their success skyrocketed after joining Saturday Night Live in 2005 as writers, with Andy debuting as a featured player. Through the exploration of the Digital Short, and following the success of ‘Lazy Sunday’, the Lonely Island became a monster in the comedy and satire music space.
I recently made the statement that the SNL’s ‘Dear Sister’ is the greatest Digital Short of all time. And a lot of people disagreed, claiming that skits like ‘More Cowbell‘ actually took top spot over the classic O.C. spoof. But considering ‘More Cowbell’ is actually a skit over a Short, I feel my statement still stands.
However everyone in the comments believed that there were so many Lonely Island songs and sketches better than ‘Dear Sister’.
So I’ve decided to rank all the best Lonely Island skit songs, from classics like ‘Lazy Day’ to more recent hits like ‘I Just Had Sex’ for your enjoyment, or disgust. We’ll find out.
10. ‘Natalie Raps’ feat Natalie Portman
The angry rapping style of Natalie Portman is a favourite with Saturday Night Live fans.
With a persona totally opposite to what we know of Natalie, the song details what a day in the life of Natalie Portman looks like. Filled with drinking, swearing, and shitting on people’s faces, the interviewer is always taken aback by Natalie’s responses.
‘Natalie Raps’ is actually the only song on this list by the Lonely Island that doesn’t actually feature any of the band members as the main character. But, the concept was so popular that we got a sequel with ‘Natalie’s Rap 2.0‘, featuring a modern rap flow, similar to Nicki Minaj, in 2018.
While the video and lyrics are funny, the song itself isn’t that strong by itself . Plus you can’t really watch the video whole bunch of times without getting over it pretty quickly, which is why it ranks so low on the list.
9. ‘Jack Sparrow’ feat Michael Bolton
‘Jack Sparrow’ is sadly one of my least favourite Lonely Island tracks, but it is like choosing a favourite child.
Don’t get me wrong, I can appreciate the concept. It’s just that ‘Jack Sparrow’ isn’t as catchy as the more modern songs on this list, which have been produced to sound like legit songs. Before you drag me, think about it. Beyond Michael Bolton’s chorus lyrics, it isn’t the most quotable song The Lonely Island has made — but it does have some great visuals.
The song is a juxtaposition between the flexy and sexy club anthem by the Lonely Island boys, and Bolton’s strange heartfelt ode to Pirates of the Caribbean, and in particular, Captain Jack Sparrow. Cinephile Michael Bolton’s switch to singing about Forest Gump, Erin Brockovich, and Scarface, however, is a definite high point.
While undoubtedly a funny video, as all Lonely Island clips are, it just isn’t a strong enough song to rank higher.
8. ‘Like A Boss’ feat Seth Rogen
Andy Samberg and Seth Rogen together is a guaranteed hit no matter what it is. ‘Like A Boss’ details Andy’s typical day of being “a boss” while doing his performance review with Seth.
Of course, there are normal boss-like activities that Andy has to do like micromanage and promote synergy, but he also details the dark side of being a boss. Like hitting on Debra, getting rejected by Debra, swallowing his sadness because of Debra, and then, naturally, shitting on Debra’s desk as payback.
The whole song is just a giant pisstake on people using the phrase “like a boss” for totally non-boss like activities.
It’s a short but sweet video that takes you on a huge journey in two small minutes, and it’s worth every confusing and captivating second.
7. ‘Threw It On The Ground’
‘Threw It On The Ground’ is the perfect song for any edgy person who hates the system… and birthday cake, I guess.
Beyond throwing an entire cake on the floor while singing “happy birthday to the ground,” heaps of things end up on the floor at the hands of an angsty Andy. Andy throws an energy drink sample on the ground for being poison and tosses a free hotdog to floor because he isn’t a charity case. After his “girlfriend” hands him a phone claiming his dad was on the line, Andy blurts out clips most iconic line: “Man this ain’t my dad. This is a cellphone.”
Half the video is just slow-mo shots of things being thrown on the ground, so the song really does live up to it’s title. Plus the cameo of Ryan Reynolds and Elijah Wood as the phony celebrities wielding tasers does give ‘Threw It On The Ground’ a couple of brownie’ points.
This artsy-at-times video comes somewhere around the middle. An undoubtedly iconic track, but not the best.
6. ‘Great Day’
Andy Samberg’s literal crackhead energy in this video clip is my kryptonite. It’s just so manic, like when Andy stops to yell at the dancers and the music returns faster after an off-camera snort? Amazing content.
‘Great Day’ follows the story of Dennis, a man destined to have exactly that — a great day. With energy fuelled by mountains of cocaine, as so subtly demonstrated by the powder residue around his nose, Dennis goes about his day.
Opening with his pigsty of an apartment, including broken cabinets, trash everywhere and gaffa taped up windows, Dennis just can’t seem to work out why he has so much energy.
“There’s a skip in my step, a pep in my pep… and I don’t know why!” Dennis sings while sniffing up the remnants of his energy booster left in his nose.
Honestly, this music video has everything. Animated birds like some sort of budget Disney film, random people dancing in the street, a mid-song flow switching to opera, and a demonic face edit. Also, Alec Baldwin and Tom Petty, just because.
Often overshadowed by bigger Lonely Island hits like ‘Dick in a Box’, ‘Great Day’ truly doesn’t, and hasn’t, gotten the recognition it deserves.
5. ‘Jizz In My Pants’
One of the earlier Lonely Island bangers, ‘Jizz In My Pants’ is a song all about premature ejaculation as the title implies.
Shifting from detailed recounts of Andy and Jorma’s unfortunate predicaments to one liners about when they accidentally bust, which turns out to be way too often, the entire video is hilarious throughout.
The facial expressions during the entire video, Akiva DJ-ing outside in the rain when Andy leaves the cinema where he watched his horror film, and the jizz over the Sixth Sense Bruce Willis twist? All iconic scenes in modern history.
Plus not only is the breakdown at the end of the song actually a genuine tune, ‘Jizz In My Pants’ is filled with so many quotable lines. My personal favourite? The entire grocery store scene:
“She looked me dead in the face and asked: ‘Cash or credit?’ And I jizzed in my pants.”
Honestly, Justin Timberlake being in the video for the sole purpose of acting as the disappointed cleaner who loves to dance just makes the entire video.
4. ‘I’m On A Boat’ feat T-Pain
Only rivalled by the musical stylings of Prestige World Wide from Step Brothers, ‘I’m On A Boat’ is undoubtedly the most popular song used to caption holiday boat party snaps. And it’s easily one of the best Lonely Island music videos.
After conveniently winning a free boat ride for three in his morning cereal box, Andy decides to take Akiva and T-Pain with him, leaving Jorma behind.
The song is simple but describes what it sets out to do. The song follows the new trio, dressed in tuxes and with T-Pain in a top hat, on a boat and recounts all the nautical adventures they have. Much to Jorma’s dismay, the entire song just describes what a great time they’re having while Jorma is stuck on land alone.
The lyrics are smart, the beat is legit, and T-Pains autotune makes ‘I’m On A Boat’ sound like an actual song. Plus, T-Pain’s musical styling throughout the song proves he’s the original king of auto-tuned ad-libs. Sorry, Migos.
3. ‘Lazy Sunday’
‘Lazy Sunday’ was produced in 2005, and like most of the older clips in this list, was created to be more of a story than a song.
Featuring Chris Parnell and Andy Samberg, ‘Lazy Sunday’ is an aggressive rap about all the lazy activities you can do on, well, a Sunday. Telling the story of their adventures on the way to watch The Chronicles of Narnia, Andy and Chris visit Magnolia Bakery, get some snacks at the deli, and answer some movie trivia at the cinema.
The video spawned the iconic line, “The Chroni-what-cles of Narnia” and is the skit that kickstarted the success of The Lonely Island and the musical Digital Short.
Sure, ‘Lazy Sunday’ is chaotic, low quality and peak-2000s, but it’s basically started this crazy journey and list, and for that we must pay our respects.
2. ‘I Just Had Sex’ Feat. Akon
A song with such impact that it sparked the male mantra that is still heard today: “Doesn’t matter, had sex.”
Arguably one of the best Lonely Island songs, ‘I Just Had Sex’ was the comedy song that defined the 2010s. And by that I mean that all males above the age of 14 would play it whenever they could. I vividly remember this song being played at parties growing up as if it was a genuine top 40 hit. Which is probably because of Akon’s vocals, which well and truly slap throughout ‘I Just Had Sex.’
The story of the video follows Andy and Jorma recounting their sexual escapades with Blake Lively and Jessica Alba, respectively. The song is just so happy and feel good that by the end of it, the originally disgusted Blake and Jessica even come onboard the idea of song.
Also, the visuals are… great? There are so many different scenes, and the rooftop sunset is actually really beautiful. Plus, there’s a cameo from John McEnroe and the video birthed the “congrats on the sex” cake gif, so do I really need to say more?
‘I Just Had Sex’ is actually the most-viewed of all Lonely Island videos, and there’s a reason for that.
1. ‘Dick in a Box’ feat Justin Timberlake
Did you really think that top spot would go to anything other than ‘Dick in a Box’?
‘Dick in a Box’ is what started the riveting Andy Samberg and Justin Timberlake musical love story that spanned over five years. People were so invested in the story that the Lonely Island released ‘Mother Lover‘ and ‘3-Way (The Golden Rule)‘, which are actually great songs. Possibly even better than ‘Dick in a Box’, but without the original there would be no sequel.
Offering their dicks in a box for Christmas in 2006, Andy and Justin really redefined romance and turned the act of gift-giving on it’s head. Literally.
Not only was the song beautifully sung, the pair even gave mid-song instructions on how to offer your loved ones your dick in a box. For any holiday. Show me any other Lonely Island song that gives you that?
For the simple fact that ‘Dick in a Box’ spawned such strong follow up videos, it is the number one Lonely Island track on this list.
Honourable mentions: ‘Boombox‘ featuring Julian Casablancas, for the boiled goose. ‘YOLO‘ featuring Adam Levine and Kendrick Lamar, for furniture being killing machines and for it being one of the best produced Lonely Island tracks. ‘Ras Trent‘ for Trent having to toil part-time at ja Cold Stone Creamery.
Michelle Rennex is a writer of semi-warm takes, a connoisseur of memes, and her dream is that one day Drake follows her back on Instagram. You can follow her bad opinions at @michellerennex.